Dailey's career started at the age of 16. His band, Slimer, were signed to Cargo Records and put on the line up for Warped tour ‘99. The deal with Cargo came into place after Tom DeLonge and Mark Hoppus from Blink-182 noticed the band as they opened a show in ‘97. Already a member of local punk bands, Dailey played his first show at 14 opening for The Queers. Slimer, disbanded after the tour to attend college. Slimer featured now well known hip-hop/reggae producer, Yeti Beats, on vocals.

In 2000, Dailey started a new band Brightlife, that were quickly signed by Capitol Records. The band featured Reed Calhoun, Tim Lopez and Nick Rucker. They recorded a self titled LP. After their A&R guy, Loren Israel, was fired the band was dropped after nine months on the road preparing for the album's release. Tim Lopez now fronts multi-platinum hit makers, Plain White T’s. Lopez is also one of the stars of NBC’s upcoming dating show, Ready For Love.

RKK entered the studio in 2007 to record the follow up album with super producer, Michael Beinhorn( Red Hot Chili Peppers, Hole, Soundgarden). Beinhorn brought in Jack Irons( Red Hot Chili Peppers, Pearl Jam, The Wallflowers) to track drums. The band also hired Fisherspooner guitarist, Sam Kearney to round out the line-up. After trouble in the studio, line-up changes and label issues. The group attempted to finish the record with producer, Jeff Saltzman( The Killers, Fisherspooner) to no avail. The band was done. The record was never released.

In 2008 Dailey was asked by Michael Beinhorn to come meet his friend who needed a bassist. That friend was Courtney Love and the band was Hole. Dailey, a lifelong fan, was excited. They went into make a record. A year and a half and four studios later, Nobodys Daughter, was released. The band signed with Jonathan Daniel at Crush Management. Hole toured the world and did all the late night shows and festivals. Dailey was rumoured to have left the group in late 2011, but is now again the full-time bassist.

They are currently working on new songs and playing shows for Courtney Love's solo career.

Dailey was asked to join, Blood Moon Therapy, in 2011. The band is fronted by, Michael Lombardi, star of the long running FX show, Rescue Me. The band did a tour for peace in Pakistan in February 2012. Working alongside The U.S. Embassy, State Department and The Humpty Dumpty Foundation, the band toured and spoke of peace and taught music masterclasses.

Shawn is also an accomplished session player. Aside from his own bands, he has worked with Jerry Harrison(Talking Heads), Scooter Ward(Cold), John Otto( Limp Bizkit) as well as producer, Ross Robinson.

On New Year's Eve 2010, Dailey got to perform alongside one of his favorite drummers, Simon Kirke( Free, Bad Company).

In 2010 Dailey performed alongside the late Ronnie Montrose at Golden Gate Park in San Francisco. They performed The Talking Heads, “Life During Wartime”, with jerry Harrison on vocals.

In 2011 he filled in on bass for The Plain White Ts on, The View.Performing their song, “Rhythm Of Love.” He also performed with his old bandmate and T’s singer, Tim Lopez, at a Christmas Charity event in his hometown of Santa Barbara. The show also featured J.R. Richards from Dishwalla.

Management/teaching/start-ups- Shawn joined Rodney Afshari’s, Inner Circle Management, in 2012 as a day to day manager. In addition to that, he is a music teacher and sits on the advisory board of musesping.com, a music industry education and network for new musicians.